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Volumn , Issue 1, 2007, Pages 115-118

Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with 1,3-cyclodiones

Author keywords

1,3 cyclodiones; Enols; Lewis acid; Methylenecyclopropanes; Ring opening reaction

Indexed keywords

ALCOHOL DERIVATIVE; ALKADIENE; CYCLOPROPANE DERIVATIVE; LEWIS ACID; METHYLENECYCLOPROPANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33846462095     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951549     Document Type: Article
Times cited : (11)

References (30)
  • 1
    • 0001487604 scopus 로고    scopus 로고
    • For the synthesis of MCPs, see
    • For the synthesis of MCPs, see: Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
    • (1998) Chem. Rev , vol.98 , pp. 589
    • Brandi, A.1    Goti, A.2
  • 4
    • 33846432658 scopus 로고    scopus 로고
    • Carbocyclic Three-Membered Ring Compounds, In Houben-Weyl, E 17a-c; de Meijere, A., Ed.; Thieme: Stuttgart, 1996.
    • (c) Carbocyclic Three-Membered Ring Compounds, In Houben-Weyl, Vol. E 17a-c; de Meijere, A., Ed.; Thieme: Stuttgart, 1996.
  • 6
    • 0344538744 scopus 로고
    • Thieme: Stuttgart
    • (e) Houben-Weyl, Vol. E 21c; Thieme: Stuttgart, 1995, 2997-3059.
    • (1995) Houben-Weyl , vol.E 21c , pp. 2997-3059
  • 19
    • 33846412882 scopus 로고    scopus 로고
    • General Procedure for the Reaction of 1,1-Diphenyl- methylenecyclopropane (1a) with 1,3-Cyclohexadione (2a) in the Presence of Sn(OTf)2. 1,1-Diphenylmethylenecyclopropane (1a, 0.30 mmol, 1,3-cyclohexadione (2a, 0.30 mmol) and Sn(OTf)2 (0.03 mmol) were dissolved in 2.0 mL of DCE. The reaction mixture was stirred at 85 °C for 4 h. Then, the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding homoallylic alcohol product 3a in 82% yield. 3-(4,4-Diphenylbut-3-enyloxy)cyclohex-2-enone (3a, Colorless solid, mp 78-79 °C. IR (CH2CU, v, 3051, 3024, 2945, 2886, 1655, 1604, 1493, 1397, 1366, 1349, 1328, 1219, 1183, 1153, 1014, 761, 701 cm-1. 1H NMR (300 MHz, CDCl3, TMS, δ, 1.93-2.01 (2 H, m, CH2, 2.34 (2 H, t, J, 6.6 Hz, CH2, 2.41 2 H, t, J, 6.6
    • 2: C, 82.99; H, 6.96%. Found: C, 82.83; H, 7.01%.
  • 20
    • 0141741420 scopus 로고    scopus 로고
    • For some other selected papers on the Lewis acid catalyzed reactions of MCPs, see: a
    • For some other selected papers on the Lewis acid catalyzed reactions of MCPs, see: (a) Shi, M.; Shao, L.-X.; Xu, B. Org. Lett. 2003, 5, 579.
    • (2003) Org. Lett , vol.5 , pp. 579
    • Shi, M.1    Shao, L.-X.2    Xu, B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.